Reaktion #1951063

Reaktionsgleichung

divinyl-phosphine oxide

benzylamine

THF

benzylamine

→

1-benzyl-4-(cyclopropylmethyl)-[1,4]azaphosphinane 4-oxide

Ausbeute 81.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated for an additional six hours at 90° C
2. 2
   EinengenThe reaction mixture was concentrated by rotary evaporation
3. 3
   Extraktionthe product was extracted into dichloromethane
4. 4
   Waschenwashed with saturated brine
5. 5
   TrocknenThe organic phase was dried with sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated by rotary evaporation
8. 8
   WaschenThe product was then eluted from the silica with ethanol
9. 9
   SonstigeThe solvents were removed by rotary evaporation

Vorschrift

Cyclopropylmethyl)-divinyl-phosphine oxide (3.56, 22.8 mmol) and benzylamine (3.0 mL, 27.4 mmol) were dissolved in a mixture of THF (100 mL) and deionized water (100 mL). The reaction mixture was heated at 90° C. for 24 hours. The reaction was not complete and so additional benzylamine (1.0 mL, 9.1 mmol) was added and the reaction mixture was heated for an additional six hours at 90° C. The reaction mixture was concentrated by rotary evaporation and the product was extracted into dichloromethane and washed with saturated brine. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was taken up in ethyl acetate and passed through a plug of silica. The product was then eluted from the silica with ethanol. The solvents were removed by rotary evaporation to yield 4.835 g of 1-benzyl-4-(cyclopropylmethyl)-[1,4]azaphosphinane 4-oxide (18.38 mmol, 81%) as an off-white crystalline solid. 1H NMR (400 MHz, DMSO) δ 7.38-7.30 (m, 4H); 7.30-7.24 (m, 1H); 3.59 (s, 2H); 2.81-2.63 (m, 4H); 1.94-1.83 (m, 2H); 1.82-1.71 (m, 2H); 1.74-1.68 (d of d, 2H); 0.96-0.83 (m, 1H); 0.56-0.49 (m, 2H); 0.22-0.14 (m, 2H); ESMS (m/z): (M+1)+ found, 264; (M+23)+ found, 286.

Quelle